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Cheap Flights from San Diego to Chicago

Compare San Diego to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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Flight deals from San Diego to Chicago

Looking for a cheap last-minute deal or the best return flight from San Diego to Chicago? If you want to travel next month, return fares start from Rs61,394. Find the lowest prices on one-way and return tickets right here.
Chicago.Rs22,991 per passenger.Departing Tue, 20 Oct.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Diego International on Tue, 20 Oct, arriving in Chicago Rockford.Price includes taxes and charges.From Rs22,991, select.
Chicago.Rs25,216 per passenger.Departing Thu, 17 Sep.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Diego International on Thu, 17 Sep, arriving in Chicago Rockford.Price includes taxes and charges.From Rs25,216, select.
Chicago.Rs25,441 per passenger.Departing Sun, 30 Aug.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Diego International on Sun, 30 Aug, arriving in Chicago Rockford.Price includes taxes and charges.From Rs25,441, select.
Chicago.Rs25,809 per passenger.Departing Mon, 2 Nov.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Diego International on Mon, 2 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs25,809, select.
Chicago.Rs31,470 per passenger.Departing Wed, 28 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Wed, 28 Oct, arriving in Chicago Midway.Price includes taxes and charges.From Rs31,470, select.
Chicago.Rs31,470 per passenger.Departing Mon, 2 Nov.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Mon, 2 Nov, arriving in Chicago Midway.Price includes taxes and charges.From Rs31,470, select.
Chicago.Rs33,518 per passenger.Departing Sat, 5 Sep.One-way flight with Alaska Airlines.Outbound direct flight with Alaska Airlines departs from San Diego International on Sat, 5 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs33,518, select.
Chicago.Rs34,922 per passenger.Departing Sat, 29 Aug.One-way flight with Alaska Airlines.Outbound direct flight with Alaska Airlines departs from San Diego International on Sat, 29 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs34,922, select.
Chicago.Rs35,661 per passenger.Departing Sat, 12 Dec.One-way flight with United.Outbound direct flight with United departs from San Diego International on Sat, 12 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs35,661, select.
Chicago.Rs38,609 per passenger.Departing Sat, 25 Jul.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Diego International on Sat, 25 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs38,609, select.
Chicago.Rs40,289 per passenger.Departing Thu, 14 Jan.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Thu, 14 Jan, arriving in Chicago Midway.Price includes taxes and charges.From Rs40,289, select.
Chicago.Rs42,799 per passenger.Departing Thu, 23 Jul.One-way flight with Alaska Airlines.Outbound direct flight with Alaska Airlines departs from San Diego International on Thu, 23 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs42,799, select.
Chicago.Rs49,713 per passenger.Departing Thu, 15 Apr.One-way flight with United.Outbound direct flight with United departs from San Diego International on Thu, 15 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs49,713, select.
Chicago.Rs49,713 per passenger.Departing Tue, 16 Mar.One-way flight with United.Outbound direct flight with United departs from San Diego International on Tue, 16 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs49,713, select.
Chicago.Rs49,713 per passenger.Departing Sun, 14 Feb.One-way flight with United.Outbound direct flight with United departs from San Diego International on Sun, 14 Feb, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs49,713, select.
Chicago.Rs49,713 per passenger.Departing Wed, 9 Jun.One-way flight with United.Outbound direct flight with United departs from San Diego International on Wed, 9 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs49,713, select.

Find the cheapest month to fly from San Diego to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like San Diego to Chicago flights are currently cheapest in October.
Jul
from Rs38,609
Aug
from Rs25,441
Sep
from Rs25,216
Oct
from Rs22,991
Nov
from Rs25,809
Dec
from Rs35,661
Jan
from Rs40,289
Feb
from Rs49,713
Mar
from Rs49,713
Apr
from Rs49,713
May
from Rs52,411
Jun
from Rs49,713

Direct flights from San Diego to Chicago

Alternative San Diego to Chicago routes

Looking for the cheapest, fastest or easiest route from San Diego to Chicago? You could fly into the following airports instead.

Chicago Midway

14km from central Chicago
Closest
from Rs31,470
Search flights

Chicago O'Hare International

25km from central Chicago
from Rs25,809
Search flights

Chicago Rockford

127km from central Chicago
Cheapest
from Rs22,991
Search flights

San Diego to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRs22,991
Cheapest month to flyOctober
Average flight time4 hrs, 9 mins
Most popular airlineAmerican Airlines
Average flights per week443

Finding cheap flights from San Diego to Chicago: Frequently asked questions

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.
The best price we found for a return flight from San Diego to Chicago is Rs51,466. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
4 hours and 9 minutes is the average flight time from San Diego to Chicago.
American Airlines, Qatar Airways and Southwest Airlines fly direct from San Diego to Chicago.
As of July 2026, there are 443 flights per week flying from San Diego to Chicago.
The cheapest month to fly from San Diego to Chicago is usually October.
If you're flying from San Diego, the cheapest airport near Chicago is Chicago Rockford – which is 126.5 km away from the centre of Chicago. We've found flights into this airport from Rs51,466.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from San Diego to Chicago on Thursday, 15 October 2026.
Yes – the average flight time is 4 hours and 9 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

In July, the average temperature is usually around 22°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
The cheapest airline that flies to Chicago is Frontier Airlines. And the cheapest airline that flies to Chicago O'Hare International Airport is Alaska Airlines.

Travelling from San Diego to Chicago: what you need to know

  • Begin planning your trip by checking out the ideal departure point for your flight from San Diego to Chicago. Explore your options for taking off from San Diego International Airport (SAN) or McClellan-Palomar Airport (CLD), two of the city's main airports.

  • The major arrival points in Chicago are Chicago O'Hare International Airport (ORD) and Chicago Midway Airport (MDW).

  • Book a direct San Diego to Chicago flight and you'll be in the air for an average of 4 hours 5 minutes.

  • The timezone in Chicago is UTC-6, which is two hours ahead of San Diego.

  • The busiest route for flights from San Diego to Chicago is San Diego International Airport (SAN) to Chicago O'Hare International Airport (ORD). Pick from 76 services connecting these two airports every week.

  • Leave enough time to make your San Diego to Chicago flight. As a general rule, turn up two hours before international departures and an hour ahead for domestic flights.

  • You can expect longer lines in popular months like August. Arriving up to four hours ahead of an international flight and two hours for domestic departures is a good idea.

How to find the cheapest flights from San Diego to Chicago

  • Don't leave things to the last minute. You're more likely to get cheap San Diego to Chicago flights if you book early. Airlines often have some great early bird discounts.

  • Getting cheap plane tickets from San Diego to Chicago is easier if you're flexible with your trip dates. Use the 'Whole month' search tool to see the best prices across every month and land an awesome deal.

  • Locking in a cheap flight from San Diego to Chicago is a piece of cake with Price Alerts. All you need to do is create one of these automatic alerts and we'll notify you as soon as there's a better deal.

  • Pick your preferred arrival and departure times, airlines and number of stops with the filters. Alternatively, sort your San Diego to Chicago flight results by 'Fastest,' 'Cheapest' or 'Best.'

Flying from San Diego

San Diego International Airport (SAN)

  • Jet off from San Diego International Airport (SAN) and fly right through to Chicago O'Hare International Airport (ORD) or Chicago Midway Airport (MDW). If you're looking for a direct flight from San Diego to Chicago out of SAN, those are your landing options.

  • These are some of the major airlines offering direct San Diego to Chicago plane tickets with departures from SAN:

  • Travelling from central San Diego to SAN takes about 25 minutes on public transport. If you ride-share, drive or take a taxi, you'll cover the 5 kilometres in 15 minutes or so, depending on traffic.

  • Need a handy hotel close to San Diego International Airport? If you're catching an early flight from San Diego to Chicago, these stays will have you sleeping moments from your departure gate:

  • 74% of flights leaving from San Diego International Airport arrive at their destination on time.

  • SAN is located at N Harbour Dr.

Arriving in Chicago

Chicago O'Hare International Airport (ORD)

  • Chicago O'Hare International Airport (ORD) to central Chicago takes about 30 minutes by car. The centre is roughly 26 kilometres away.

  • When travelling on public transport, expect a journey time of roughly 45 minutes.

  • If you're arriving on a late flight from San Diego to Chicago, few things beat the convenience of staying close to the terminal. Pick up your bags from the carousel and then be showered and relaxing not long after at one of these hotels near ORD:

  • Pick up a Chicago O'Hare International Airport rental car and discover Chicago and beyond with your own wheels. Routes Car Rentals, Dollar and Budget are leading providers you can book with here.

  • Booking your vehicle from Chicago O'Hare International Airport about four weeks ahead boosts your odds of scoring a great price.

  • ORD is situated at 10000 West O'Hare.

Chicago Midway Airport (MDW)

  • Chicago Midway Airport (MDW) is roughly 14 kilometres from central Chicago. Once you've disembarked your flight from San Diego to Chicago, it takes approximately 25 minutes to reach the heart of the city in a taxi or ride-share.

  • If you hop on public transport, the ride to the centre will take you 30 minutes or so.

  • You'll find some great places to call home for the night near MDW. Tuck yourself in after your San Diego to Chicago flight at one of these perfectly located options:

  • The quickest way to get to where you're going is with a Chicago Midway Airport rental car. Grab your wheels from Dollar, Hertz or Budget and be on your way in a flash.

  • Call dibs on the best options. Reserving your ride from MDW four weeks in advance often means better prices and a bigger choice of vehicles.

  • Chicago Midway Airport is located at 5700 South Cicero.

Chicago Rockford Airport (RFD)

  • Chicago Rockford Airport (RFD) is about 129 kilometres from central Chicago. It takes about 1 hour 40 minutes to get to the city centre in a ride-share or taxi once you've stepped off your flight from San Diego to Chicago.

  • Public transport can get you there in about 2 hours.

  • Start your trip without stressing about how to get to your next stop with a Chicago Rockford Airport rental car. Book your ideal wheels with reliable suppliers here like Budget, Alamo and National.

  • If you're hoping for a particular make or model, booking early increases your chances of snagging what you want. Reserve your ride from RFD at least a couple of weeks ahead of your flight from San Diego to Chicago.

  • The address for Chicago Rockford Airport is 2 Airport Cir.

Best time to go to Chicago

  • March is the quietest month for flights from San Diego to Chicago, while July is the most popular. Figure out the ideal time to go to Chicago based on whether you like a lively atmosphere or a more laid-back vibe.

  • Lock in a San Diego to Chicago ticket departing in July if you're eager to experience the city during its warmest month. You can expect temperatures in Chicago to range from 16ºC to 28ºC.

  • January sees average temperatures of between -12ºC and 3ºC. Look for cheap flights from San Diego to Chicago around that time if you like travelling in cooler conditions.

More about Chicago

Explore more of the United States

  • You've seen Chicago, now it's time to explore other corners of the United States. Journey about 451 kilometres southeast to Columbus to tick off its leading sights. From Franklin Park Conservatory and Botanical Gardens to Columbus Park of Roses and Ohio Theatre, you'll have a packed itinerary ahead.

  • Indianapolis is another favourite destination in the United States and is around 257 kilometres southeast of Chicago. No journey is complete without visiting Lucas Oil Stadium, Eiteljorg Museum of American Indians and Western Art and The Children's Museum of Indianapolis.

More travel options

Plan the rest of your trip from San Diego to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.